Total synthesis of Isosteviol:
| Reference: | Snider, B. B.; Keselgof, J. Y.; Foxman, B. M. J. Org. Chem. 1998, 63, 7945. DOI |
| Reactions: | Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • Alkene cleavage • Carbocupration Alkyne • Cu-Allyl+Alkyne • Mg-R → Cu-R • Li-Allenyl/Propargyl+Alkyl-X • Allyl-X+Li-R • Wittig-carboxymethyl → EnoateEster • KetoEster dianion+Alkyl-X • Allyl-X+Enolate • Hydrogenation alkene • Alkyl-OH → Alkyl-H(2°) • Allyl-X → Allyl-Br • CarboxEster enolate+Alkyl-X • Allyl-X+Enolate • Dehydration → Ene • Li-Alkynyl+Aldehyde • Li/H → Li-Alkynyl • Allyl-OH → Allyl-Br • O-H → O-SO2Me • Allyl-X → Allyl-Br • Finkelstein reaction • Lemieux-Johnson oxidation • KetoEster → Ester • Radical cyclization(α-Keto) • Cyclohexanone • Cyclopentane • Bicyclo(440) • Bicyclo(321) • CarboxEster → Alkyl-OH • Alkyl-OH → CarboxAcid • Jones oxidation • CarboxEster → Alkyl-OH • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • O-H → O-SO2Me • |
| Reagents: | BuLi(n) • Allenyl-Li • Alkynyl-Li • Allyl-Cl • Formaldehyde • CuI • Sulfonyl chloride, methane, NEt3 • LiNiPr2 • AlH4-Li+ • Cr2O7·2PyH (PDC) • PPh3=C(Me)-CO2R • AlH4-Li+ • Sulfonyl chloride, methane • Acetoacetate • NaH • BH4-Na+ • OsO4, NaIO4 • PPh3, DEAD • H2, Pt • AlH4-Li+ • CrO3, H2SO4 (Jones) • Allyl-MgX • CuI • BuLi(n) • Bromide, lithium • HMPA (solvent) • Mn(OAc)3 • Cu(OAc)2 • CH2=C(OLi)(OR) • |